Still a little bleary eyed, I push the lid down on my cappuccino and leave Fools & Horses, headed for downtown. It's Saturday morning, and I'm taking the photographs of seven fashionable Winnipegers over six hours. Each has pulled pieces from their wardrobe to create a holiday party look. I'm about to spend the day taking photographs and talking about clothes, so despite a lack of sleep, I'm feeling giddy.

I arrive at a mixed-use building on Donald a few minutes ahead of schedule. Painter Michael Sawatzky lets me in. We chat about our days, and I look at some of his work while we wait for Sara Clark. When she arrives, we hike up the stairs to the studio space she shares with Tonychestnut's Jill Sawatzky on the top floor.

I brew coffee while Sara changes. Jill arrives to continue working on pieces for that night's pop-up at Freshair Boutique. Over the course of the day, I sip coffee and snack on chocolate chip cookies. Conversations range from social media presence and responsibility, to upcoming plans, to evolving wardrobe practices.

When I pack up my things and wave goodbye to Jill - still busy at her sewing machine - I'm worn out but content. Making my way back down the creaking steps, I look forward to a quick dinner, a long nap and an evening of work that allows me to relive the day.

Sara wears a dress by Tonychestnut, shoes by Jeffrey Cambell, and the earrings she wore on her wedding day.

SC: I found the shoes on sale from Urban Outfitters. The block heel makes them so much more comfortable.

The Tonychestnut little black dress had the great little shoulder detail on it originally. I made the mistake of putting it through the wash. Jill told me to take them off after that, and she'd make me some new ones. We never got around to it, but it’s great, because I like it this way too.

The earrings I actually wore for my wedding when I was in New Orleans. I don’t even remember where I got them. They’re sparkly and not something I usually wear, but they’re perfect for holidays and special occasions.

I love this outfit because it’s comfortable. I can walk in these shoes, the dress doesn’t cling anywhere, and I don’t have any weird elastic marks. It just feels good: like a soft little tent.

Hanna wears a dress from Urban Outfitters, vintage mules from Nettie + Min, and a thrifted coat and purse.

HR: I’d been eyeing the dress online for a million years, but it was $200. I found it on a sale rack for fifty. I drop all my money verticle stripes. The shoes are Nettie + Min. The label says they’re from Eaton's.

I love thrifting, but I need to be better about finding a place to put all the stuff I don’t wear anymore. Sometimes I buy things because they’re just $5, and I end up with a lot of stuff.

I found the purse at a Salvation Army near my house, then added the fringe myself. I can’t sew, so I cheated my way around it with a hot glue gun. I also have a pair of jeans that I cropped, then glued fringe to. I always get made fun of when I wear them, but I don’t care. It reminds me of one of the characters from the “Don’t Hug me I’m Scared” videos. It’s really silly.

Stephanie wears a dress by Hayley Elsaesser and shoes by Fleuvog. Connor wears a thrifted turtleneck and pants with Doc Martens.

SPB: I got the Hayley Elsaesser dress at her shop in Toronto. She only puts out two or three collections a year, and they’re very fun with prints like snakes and magic 8-balls. I visited the store because of an outfit that I saw in a Lowell video called “I Love you Money.” It’s a two-piece body-con with a print that says “Heavenly” all over. It was sold out in my size, so I tried on a bunch of other body-con pieces. When I got home, I ordered this on sale online, because I’m a Winnipeger, and that’s how we do it.

I’m wearing some hand-me-down Fleuvogs. Fleuvogs are my favourite. My mom used to have a lot of pairs of them, and I was always jealous of her, but now I feel like I’ve caught up. One of my favourites was a pair of red, Mary Janes with a little white ribbon embroidery, RIP. I wore them literally into the ground; my heels would touch the ground. I refused to stop wearing them for so long. I still think about them all the time. My mom took them away and they were gone for like a year, and then I found them again, and she took them back!

CB: These pants are Versace I got from the Goodwill. The turtleneck is from the Goodwill as well. There’s one by my work on Sargent that I go to pretty much every day in some capacity, even just for 5 minutes before work starts, or on a break or something. I can go in, and know exactly what’s there. There’s no looking through garbage. There are constantly designer brands at that Goodwill, but I think a lot of them are fake.

And these are my Docs that I wear every day.

Malaikah wears a fur vest by Hudson's Bay Company, a jumper by Kit and Ace, a necklace by Aldo accessories, and ankle boots by Spring.

MR: I generally avoid wearing makeup to holiday parties, because I know if I’m in a festive setting, I’m going to be very rambunctious. The outfit is comfortable; I want to have a good time. Makeup becomes a stressor. If I get photos back, I just see that I sweated through my makeup. And that’s fine because I danced up a storm, but the makeup's not helping, it’s hindering.

This is one of my favourite necklaces. I really like big necklaces with a geometric feel. I always get my necklaces at Aldo accessories, because no one wants to buy the crazy ones, so they go on sale really quickly. I got this for $9.

A fur vest is the quintessential winter staple for me. I like it because it adds warmth, but it looks nice. It was the solution to me trying to figure out how I can be warm without throwing off my outfits.

I don’t usually wear dark colours, but over the holidays I want to go more sophisticated with little black dresses or this black and navy jumper. There’s glitter everywhere this time of year, I don’t need to add to it. I like these because they’re wide-legged, so even in winter, I can wear wool tights and be really warm, but it won’t throw off the line at all.

AC: I don’t feel like I put a lot of effort into what I buy. I’ve been buying and collecting clothes for a very long time, and I’m now trying to reevaluate that a bit and figure out what that can look like. But I’m still in the same patterns and habits. My first job was at Value Village when I was sixteen. I’d see great things that I couldn’t leave, but I also couldn’t really see myself wearing them. Now I’m trying to transition that into a business and channel it positively. I love the idea of having a very streamlined, well-curated closet, but I don’t have that yet. I do find myself going to the same pieces in my closet over and over again though.

The pants are Forever21. I have patience in stores like that. I find things that look great, look expensive. I try not to spend too much time or money there, but I check out the crazy sales; these were $4.

The shoes are Acne. I had a time in my life when I was very lucky with a shoe website showing interest in me, and they would send me shoes. I have a very nice shoe collection because of them.

The turtleneck was one of those end-of-winter-season things, grocery shopping and you go by the back, and it’s turtlenecks for $3.94. There's a weird bleach stain on one sleeve, and I don’t know if it was me, or if I bought it like that and that’s why it was on sale, but it’s something I’ve grown fond of. It's a weird imperfection, but in the sea of black in my dresser I can see this, and I know what I’m pulling out.

The vest is vintage. It's practical in Winnipeg, where putting an extra layer on anything helps. I used to work at a grocery store, and vests like these are exactly what you throw on when you get a box from the freezer. I love taking things out of their intended purpose and pairing them with more formal stuff. I find myself doing that often. Another one of my favourite shirts right now is an extra large, snap button work shirt. It’s from someone who worked in a body shop. I'll build a uniform around that. I like taking something and flipping its intention.

Mackenzie wears boots by Red Wing, hand-me-down pants by Norse Projects, and a shirt and button-up by Corue.

These are Red Wings that I picked up with my partner Sarah. We drove down to Chicago just to go, and we stopped in Red Wing, Minnesota at the boot factory. It was a random detour to get these boots. I like wearing leather and wool at all times. It’s just comfortable and durable and will show age and character. Caring for leather goods is real swell.

I got these pants from my old landlord. When I went to Nunavut, he was going to take care of my air plants. I had a few hundred dollars worth of air plants, and he watered them once. I came back to rotting, dried air plants in my space. So pants for plants. They’re durable wool. He wore them in, busted off the buttons, I resewed them all and then started wearing them. I like passing down and trading clothes. My partner Sarah and I will wear each other’s clothes a lot too. I love seeing how she incorporates my pieces into her wardrobe.

The Corue is all organic, Japanese cotton, and all made in Winnipeg. It’s comfortable and light and it’s what I want: ethically sourced fabrics, clothes that were made here. I can support my friends who are making these things. The flannel is Japanese cotton twill with mother-of-pearl buttons. I’ll wear Corue with anything because it’s durable and lasts. I’m not going to wear something I can only wear once. I want to be able to wear everything I own into the ground.

A huge thank you to all the models for volunteering their time, and to Sara Clark, Jill Sawatzky and Rachael Thorleifson for allowing me to photograph in their beautiful spaces. This piece is intended to highlight a love of fashion and self expression. None of it is sponsored in any way, and the people involved did not receive financial compensation for the pieces they wore.